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Located in the heart of Duval St, this unique property offers a central location to the Key West landmarks and sights. Enjoy all Key West has to offer from a historic building with a private balcony overlooking Duval St. This property features a 1 bedroom with a king size bed, full bath and...

Upper Duval is the best! A few steps away from the Southernmost pt &amp; beaches,great restaurants,art galleries, Louies backyard,and Blue Heaven. A few more steps from Mallory sq, Sloppy Joes, Smokin tuna, the pier restaurants, entertainment day and night. Have the best of both worlds, be in the...

La Dolce Vita is just steps to Duval Street!
&#39;La Dolce Vita&#39; is beautiful and is a totally renovated condo.
Please check out our calendars for availability, photos and video.
Everything is brand new from floor to ceilings! 14 foot high ceilings with back lit crown molding in every room...

This 1200 sq ft luxury apartment in the the heart of Old Key West is located only 2 blocks off Duval St and is a short walk or bike to all the fun of Key West ! Very quiet street with no through traffic. The property is completely private and safe, surrounded by a 6 foot gated fence and tropical...

Bring the whole family together for a reunion or holiday celebration at this spacious, Key West home located just a block from the non-stop fun of Duval Street. This rental, with space for up to 10 guests, features an enclosed yard, private pool, furnished patio, and off-street parking for two...

OVERVIEW
The Cigar House is a 100+ year old Cigarmaker&#39;s house. The house is recently renovated, charming, spacious, secluded and private. The house can comfortably accommodate a maximum of four (4) guests, who are comfortable sharing an open sociable living environment - (1) queen bed, (1) queen...

Perfect for an extended family or group of friends, this property offers great amenities including private pool, and close proximity to many Key West attractions!
CASA GRANDE: You hear all the time about grand homes tucked away in little private corners of Key West; this is one of them. Located...

Up to four guests can enjoy all the fun of Key West at this updated home complete with a shared pool with waterfall, and lush, outdoor seating area. As an added bonus, this home comes with private, off-street parking for one vehicle - a real luxury in the Keys! Dogs are allowed for a small nightly...

OVERVIEW
The Conch House is a 100+ year old Cigarmaker&#39;s house. The house is recently renovated, charming, spacious, secluded and private. The house can comfortably accommodate a maximum of five (5) guests, who are comfortable sharing an open sociable living environment - (1) queen bed, (2) twin...

Located in the middle of Duval St, you are a 15 minute walk in one direction to the Atlantic Ocean and the Southernmost Point, and the same distance to the Gulf of Mexico and Mallory Square. Shopping, nightlife and the best restaurants are outside your front door. Hemingway House is 2 blocks away!...

Our Old Town Eyebrow has an ideal location on the island of Key West! Only 1 1/2 blocks from the famous Duval Street but set back in a quiet, comfortable neighborhood for you to enjoy your time with loved ones. Stunning views of the Key West Light house greet you as you enter our home.
The unique...

In the midst of many historic sites this home has all the updated amenities for you and your family to enjoy plus be within walking distance of the Southernmost Point.
This timeless private conch home just steps away from the Hemingway House and the Key West Lighthouse a perfect location to be...

Check out the new &#39;Duval Loop&#39; that ferries you around Old Town for free and is located at the corner of this homes block!!!!Map is included in pictures. Hemmingway House, Lighthouse, Butterfly World, Southern Most Point, Conch Tour Train, Beach, Galleries &amp; Restaurants are all located within a 5...

Location! Location! Location! Duval Breeze offers the best location in town! Walking distance to restaurants, bars and galleries and easy biking distance to the beaches!
Enjoy the great location of this beautiful 2 bedroom 2.5 bath vacation home key west located in the gated rooftop community...

Lounge your days away by the pool or enjoy the peace and quiet away from the hustle and bustle of Duval Street.
Located in one of Key West’s historic and most cultural neighborhoods this lovely condominium will give you cause to celebrate the island way of life. A fabulous location that will allow...

Privacy meets convenience at this beautiful Key West vacation rental, which features a two-bedroom, two-bathroom home, a separate studio cottage, a private pool, and room for up to eight guests. The family dog is also welcome to join you for an additional nightly fee.
This recently renovated...

OVERVIEW
The Turtle House is a 100+ year old recently completely renovated historic house. The house can comfortably accommodate a maximum of five (5) guests, who are comfortable sharing an open living environment - (1) queen bed, (1) full bed, (2) queen sleeper sofas.
The house can be described...

This 4BR/1.5BA tropical retreat is situated in a lush gated community, enveloped by Spanish lime trees, hibiscus, orchids, and a wide variety of beautiful species and exotic palms.
In a prime locale, you’ll be within minutes of everything Old Town Key West has to offer. Walk to the beach or hop...

Cozy, comfortable, affordable. Not to mention a location in the very heart of the Historic District of Upper Duval. That&#39;s why this one bedroom/one full bath rental is aptly named Bella Vita, the beautiful life. Located within La Casa de Luces building, Bella Vita features a wrap-around porch, a...

BOWE CONCH HOUSE (monthly rental): The Bowe Conch House has evolved within the Thomas family, Conchs, born and raised in Key West, for more than 4 generations. Prior to buying the house in the 1930&#39;s for $2,500, George and Ethel Bowe-Thomas lived across the street paying $3.00 per month for rent!...

Poinciana House, a one-bedroom, two-full bath conch cottage, is a standout in authentic Florida design and guest friendliness. The private pool area and tropical garden is where you find the namesake Royal Poinciana tree complete with a chair hammock beckoning from one enormous branch. Swinging...

Would you enjoy truly modern luxury within walking distance to Key West&#39;s best restaurants, clubs, and art galleries? If so, this is the vacation house for you! We are set within Key West&#39;s Historic District, a block from famous Duval Street, 2 1/2 blocks from the Hemingway House, 7 blocks to...

Lush tropical outdoor setting within this small compound, privacy as you enjoy the pool and outdoor gardens.
Located in one of Key West’s historic and most cultural neighborhoods this lovely condominium will give you cause to celebrate the island way of life. A fabulous location that will allow...

Affectionately known as the Captain’s Quarters, this two-story custom-built 3BR/3BA is located on a quiet lane in Bahama Village. This lovely neighborhood exudes a charming old Key West vibe. Please inquire for options.
Step out to your back yard for a dip in the private pool, set amid lush...

This family-friendly Key West home features five separate villas grouped together, a shared pool, and a location that puts you close to all of the action.
Notice: This is in a residential area, Quiet Hours are 10:00pm- 8:00am
Located on Center Street, this home is just a mile from the Key West...

I must confess, there’s something about walking along an exotic tropical pool-garden path that sends me to an instant state of calm. Palm fronds gently dancing in the breeze, orchids hanging in the trees, manicured gardens, a pristine swimming pool set with comfortable lounge chairs. This is what...

2017 Historic Preservation Award Winner!
This licensed vacation home was recently featured on Key West&#39;s historic home tour and is available to rent monthly. We recently completed a massive 6-month remodel, making this one of the more spectacular vacation homes you&#39;ll find for rent in Old Town. In...

Enjoy this beautifully remodeled home with quaint charm and colorful front and back porches. Take in the lush landscaping that surrounds the one-of-a-kind lazy river heated pool, or relax in the well-designed interior. This home features Key West flair, two workstations, two bicycles, ceiling fans,...

Take your romantic getaway at this bright studio condo in the heart of Key West&#39;s historic Old Town! Free WiFi, a deck, and a kitchenette will have you feeling right at home less than a mile from the beach.
Visit Fort Zachary Taylor State Park &amp; Beach, about a mile away, where you&#39;ll find white...

You know that incredible experience of Déjà vu? When you enter someplace for the very first time, and instantly you get that sense that you’ve been there before? When I first visited this vacation rental house, it happened to me. My mind sparked, the place seemed wonderfully familiar, and I felt an...

Find a colorful, comfortable escape in the heart of Key West at this two-bedroom condo, where you&#39;ll enjoy a private deck and balcony, a community swimming pool, and easy access to beaches and downtown.
This well-appointed condo sits in the heart of historic Key West, mere steps from the Duval...

A large group getaway to Key West starts with this pair of charming cottages, which feature a total five bedrooms, three-and-a-half bathrooms, and a max occupancy of 16. The property also includes a private heated swimming pool, a private hot tub, and dog-friendly accommodations.
The cottages sit...

OVERVIEW
The Main House is a (2) story 100+ year old, recently completely renovated Conch house. The design of this property lends itself perfectly to small gatherings of families and friends.
The house can comfortably accommodate a maximum of ten (10) guests - (1) queen bed, (1) full bed, (1)...

If Key West is on your travel itinerary, make this lovely rental for six your home away from home and spend your time lounging by your private pool and spa.
Located in Historic Bahama Village, this home is one block away from the world-famous Duval Street, where you can enjoy galleries, shops,...

Ready to escape to Key West? Make the most of your visit and stay at Top of Duval Vacation Rentals, located in the heart of Key West&#39;s Old Town. It&#39;s like having your own private hotel.
If you are vacationing with family and friends, Top of Duval offers a truly unique layout with six individual...

Our lovely home is rented for a 28 day minimum.Enjoy the lovely Key West ocean breeze from your private Tree House. Two Blocks to Blue Heaven, 4 blocks to the beach, 3 blocks to Duval, 3 blocks to the biggest pool on the Island, you will not find a better or quieter location to enjoy all that Key...

Key West has long been loved for its playful spirit, forever attracting all genres of fun-loving artists, musicians, and writers. In recognition for the island’s historical humor, we have fondly named this beautiful upscale home, On Hemingway’s Rounds. Paying tongue-in-cheek homage to Papa’s...

This sensational vacation home provides three bedrooms, two and a half baths, pool, and a downtown location yet manages to create a serene, get-away-from-it-all feel. Called Hemingway&#39;s Library, the residence maintains the mystique of the island&#39;s most famous author by way of books, pictures, and...

Experience the best of Key West from the comfort of this charming studio-style cottage. A private hot tub, dog-friendly accommodations, and modern conveniences including free WiFi and a shared washer/dryer make this vacation rental perfect for everything from a laid-back retreat to an...

There&#39;s no more perfect place to practice the art of tropical vacationing than this professionally decorated, two-story townhome, which features two bedrooms, two and a half baths, a private deck with private hot tub, and a master bedroom balcony. A short walkway flanked by lush gardens leads to a...

Enjoy that next romantic getaway in Key West at this adorable and colorful ground-floor studio complete with a well-equipped kitchenette and view of the well-maintained courtyard and shared heated pool. Please note that off-street parking is available at this address.
Take a short stroll over to...

Without a doubt, one of the rarest private Key West vacation cottages available. Situated in one of the most requested locations in Old Town Key West, this luxury renovated turn-of-the-century Vintage Luxury Cottage vacation rental is hidden just off upper Duval Street in Old Town. Enter the gate...

Immerse yourself in the island lifestyle when you book this Key West accommodation, comprised of a two-bedroom house and a separate one-bedroom pool house. Featuring a private heated pool, a private parking spot, and an outdoor shower, this home gives you the chance to unwind. Four dogs are...

The sunny paradise of Key West beckons, and this dog-friendly home is the perfect place to stay, with a private patio and hot tub ensuring relaxation is never far away.
Located just steps from desirable Duval Street, this home makes it easy to experience all the best attractions in Key West, from...

Escape to Key West with the family at this charming Floridian home on a quiet street with a furnished patio, private, heated swimming pool, and space for up to six guests and a dog for a small nightly fee. This home also offers off-street, private parking for one vehicle.
Located alongside several...

A sun-soaked getaway in the Florida Keys awaits you when you stay at this beautiful dog-friendly vacation rental! Lounge in comfort by the private pool or stay inside and enjoy the air conditioning while you browse the cable channels on the flatscreen TV. However you spend your vacation days,...

Experience a quintessential Key West vacation when you stay at this historic three-bedroom, two-and-a-half-bathroom cottage. With a private heated pool, home comforts including free WiFi and cable TV, and room for up to eight guests, this home is perfect for a large family or a group of close...

Stay in style in the heart of Key West&#39;s historic downtown, where you&#39;re steps from the beach and all Duval Street has to offer! Your back patio houses a private hot tub, dog-friendly accommodations, and grill, perfect for lounging with the group after a long day of play.
You&#39;re located on...